Application of enantioselective Heck-Matsuda reactions in the synthesis of densely functionalized cyclopentenols

Resumo

With the progress on the enantioselective arylation of 3-cyclopentenol obtained by our group, the present project was motivated to explore new possible substrates for the enantioselective Heck-Matsuda reactions (EHM) and try to propose new synthetic routes for tricyclic skeletons, found in tromboxan inhibitors and other related pharmaceuticals. In this project, 2-substituted derivatives of 3-cyclopentenol were prepared from cyclopentadiene epoxide using substituents like ethyl, cyanomethyl and esthers, and evaluated as substrates for EHM. After evaluation and optimazation of reaction conditions, it was possible to obtain satisfactory yields, isolate and characterize different arylation products using techniques as HPLC, GCMS and NMR, providing a better understanding of the reaction scope and EHM applications.